diff --git a/.changeset/gorgeous-monkeys-remain.md b/.changeset/gorgeous-monkeys-remain.md
new file mode 100644
index 0000000000..f9bbb669f2
--- /dev/null
+++ b/.changeset/gorgeous-monkeys-remain.md
@@ -0,0 +1,6 @@
+---
+'@backstage/techdocs-common': patch
+---
+
+Add more context to techdocs log lines when files are not found along with
+ensuring that the routers return 404 with a descriptive message.
diff --git a/packages/techdocs-common/src/stages/publish/awsS3.test.ts b/packages/techdocs-common/src/stages/publish/awsS3.test.ts
index dbc81a25b4..35bc80438b 100644
--- a/packages/techdocs-common/src/stages/publish/awsS3.test.ts
+++ b/packages/techdocs-common/src/stages/publish/awsS3.test.ts
@@ -352,5 +352,16 @@ describe('AwsS3Publish', () => {
         'content-type': 'text/plain; charset=utf-8',
       });
     });
+
+    it('should return 404 if file is not found', async () => {
+      const response = await request(app).get(
+        `/${entityTripletPath}/not-found.html`,
+      );
+      expect(response.status).toBe(404);
+
+      expect(Buffer.from(response.text).toString('utf8')).toEqual(
+        'File Not Found',
+      );
+    });
   });
 });
diff --git a/packages/techdocs-common/src/stages/publish/awsS3.ts b/packages/techdocs-common/src/stages/publish/awsS3.ts
index 85857929d5..f2e1b867ec 100644
--- a/packages/techdocs-common/src/stages/publish/awsS3.ts
+++ b/packages/techdocs-common/src/stages/publish/awsS3.ts
@@ -351,8 +351,10 @@ export class AwsS3Publish implements PublisherBase {
 
         res.send(await streamToBuffer(stream));
       } catch (err) {
-        this.logger.warn(err.message);
-        res.status(404).json(err.message);
+        this.logger.warn(
+          `TechDocs S3 router failed to serve static files from bucket ${this.bucketName} at key ${filePath}: ${err.message}`,
+        );
+        res.status(404).send('File Not Found');
       }
     };
   }
diff --git a/packages/techdocs-common/src/stages/publish/azureBlobStorage.test.ts b/packages/techdocs-common/src/stages/publish/azureBlobStorage.test.ts
index 914cc24986..cace6caae8 100644
--- a/packages/techdocs-common/src/stages/publish/azureBlobStorage.test.ts
+++ b/packages/techdocs-common/src/stages/publish/azureBlobStorage.test.ts
@@ -375,5 +375,16 @@ describe('AzureBlobStoragePublish', () => {
         'content-type': 'text/plain; charset=utf-8',
       });
     });
+
+    it('should return 404 if file is not found', async () => {
+      const response = await request(app).get(
+        `/${entityTripletPath}/not-found.html`,
+      );
+      expect(response.status).toBe(404);
+
+      expect(Buffer.from(response.text).toString('utf8')).toEqual(
+        'File Not Found',
+      );
+    });
   });
 });
diff --git a/packages/techdocs-common/src/stages/publish/azureBlobStorage.ts b/packages/techdocs-common/src/stages/publish/azureBlobStorage.ts
index 4dfd8ba2f5..2d3df4e6b4 100644
--- a/packages/techdocs-common/src/stages/publish/azureBlobStorage.ts
+++ b/packages/techdocs-common/src/stages/publish/azureBlobStorage.ts
@@ -328,8 +328,8 @@ export class AzureBlobStoragePublish implements PublisherBase {
       const fileExtension = platformPath.extname(filePath);
       const responseHeaders = getHeadersForFileExtension(fileExtension);
 
-      try {
-        this.download(this.containerName, filePath).then(fileContent => {
+      this.download(this.containerName, filePath)
+        .then(fileContent => {
           // Inject response headers
           for (const [headerKey, headerValue] of Object.entries(
             responseHeaders,
@@ -337,11 +337,13 @@ export class AzureBlobStoragePublish implements PublisherBase {
             res.setHeader(headerKey, headerValue);
           }
           res.send(fileContent);
+        })
+        .catch(e => {
+          this.logger.error(
+            `TechDocs Azure router failed to serve content from container ${this.containerName} at path ${filePath}: ${e.message}`,
+          );
+          res.status(404).send('File Not Found');
         });
-      } catch (e) {
-        this.logger.error(e.message);
-        res.status(404).json(e.message);
-      }
     };
   }
 
diff --git a/packages/techdocs-common/src/stages/publish/googleStorage.test.ts b/packages/techdocs-common/src/stages/publish/googleStorage.test.ts
index 4247442c54..0190128e6c 100644
--- a/packages/techdocs-common/src/stages/publish/googleStorage.test.ts
+++ b/packages/techdocs-common/src/stages/publish/googleStorage.test.ts
@@ -351,5 +351,16 @@ describe('GoogleGCSPublish', () => {
         'content-type': 'text/plain; charset=utf-8',
       });
     });
+
+    it('should return 404 if file is not found', async () => {
+      const response = await request(app).get(
+        `/${entityTripletPath}/not-found.html`,
+      );
+      expect(response.status).toBe(404);
+
+      expect(Buffer.from(response.text).toString('utf8')).toEqual(
+        'File Not Found',
+      );
+    });
   });
 });
diff --git a/packages/techdocs-common/src/stages/publish/googleStorage.ts b/packages/techdocs-common/src/stages/publish/googleStorage.ts
index 1f519829f2..ba5bec8752 100644
--- a/packages/techdocs-common/src/stages/publish/googleStorage.ts
+++ b/packages/techdocs-common/src/stages/publish/googleStorage.ts
@@ -261,10 +261,12 @@ export class GoogleGCSPublish implements PublisherBase {
           res.writeHead(200, responseHeaders);
         })
         .on('error', err => {
-          this.logger.warn(err.message);
+          this.logger.error(
+            `TechDocs Google GCS router failed to serve content from bucket ${this.bucketName} at path ${filePath}: ${err.message}`,
+          );
           // Send a 404 with a meaningful message if possible.
           if (!res.headersSent) {
-            res.status(404).send(err.message);
+            res.status(404).send('File Not Found');
           } else {
             res.destroy();
           }
diff --git a/packages/techdocs-common/src/stages/publish/openStackSwift.test.ts b/packages/techdocs-common/src/stages/publish/openStackSwift.test.ts
index 84007c0f5b..8dde687997 100644
--- a/packages/techdocs-common/src/stages/publish/openStackSwift.test.ts
+++ b/packages/techdocs-common/src/stages/publish/openStackSwift.test.ts
@@ -364,5 +364,21 @@ describe('OpenStackSwiftPublish', () => {
         'content-type': 'text/plain; charset=utf-8',
       });
     });
+
+    it('should return 404 if file is not found', async () => {
+      const {
+        kind,
+        metadata: { namespace, name },
+      } = entity;
+
+      const response = await request(app).get(
+        `/${namespace}/${kind}/${name}/not-found.html`,
+      );
+      expect(response.status).toBe(404);
+
+      expect(Buffer.from(response.text).toString('utf8')).toEqual(
+        'File Not Found',
+      );
+    });
   });
 });
diff --git a/packages/techdocs-common/src/stages/publish/openStackSwift.ts b/packages/techdocs-common/src/stages/publish/openStackSwift.ts
index 2902d7384f..b5111ec2fb 100644
--- a/packages/techdocs-common/src/stages/publish/openStackSwift.ts
+++ b/packages/techdocs-common/src/stages/publish/openStackSwift.ts
@@ -245,10 +245,15 @@ export class OpenStackSwiftPublish implements PublisherBase {
 
           res.send(await streamToBuffer(stream));
         } catch (err) {
-          this.logger.warn(err.message);
-          res.status(404).send(err.message);
+          this.logger.error(
+            `TechDocs OpenStack swift router failed to serve content from container ${this.containerName} at path ${filePath}: ${err.message}`,
+          );
+          res.status(404).send('File Not Found');
         }
       } else {
+        this.logger.error(
+          `TechDocs OpenStack swift router failed to serve content from container ${this.containerName} at path ${filePath}: Not found`,
+        );
         res.status(404).send('File Not Found');
       }
     };